C1C2C(=CC=CC=2)C=CC=1.[Li].[C-]1C2C(=CC=CC=2)C=CC=1.[Li+].[CH3:23][N:24]1[C:33]2[C:28](=[CH:29][C:30]([O:34][C:35]3(SC4C=CC=CC=4)[CH2:37][CH2:36]3)=[CH:31][CH:32]=2)[CH2:27][CH2:26][C:25]1=[O:45]>C1COCC1.C(OCC)(=O)C.O>[CH:35]1([O:34][C:30]2[CH:29]=[C:28]3[C:33](=[CH:32][CH:31]=2)[N:24]([CH3:23])[C:25](=[O:45])[CH2:26][CH2:27]3)[CH2:36][CH2:37]1
Naphthalene (1.0 g, 7.85 mmol) was dissolved in THF (7.5 ml) under nitrogen and freshly cut lithium metal (54 mg, 7.85 mmol) was added. The mixture was stirred at room temperature until a dark green solution of lithium naphthalenide was obtained. This solution was cooled to −78° C., then 1-Methyl-6-(1-phenylsulfanyl-cyclopropoxy)-3,4-dihydro-1H-quinolin-2-one (170 mg, 0.53 mmol) in THF was added over 1 minute. The reaction was stirred for 17 minutes and then water and ethyl acetate were added. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic extract was dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography using 30% ethylacetate/hexane to give the title compound (42 mg, 36% yield).
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